Ethanolamine → HCID 67168446, compound

Participants

Reaction Steps

To 2-hydroxy-2-(2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazol-7-yl)acetic acid (Preparation 84C, isomer 2, 0.035 g, 0.074 mmol) in DMF (1 mL) were sequentially added N-methylmorpholine (0.033 mL, 0.296 mmol), 2-aminoethanol (5.81 μl, 0.096 mmol) and HATU (0.042 g, 0.111 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with 0.5 mL of MeOH and subjected to preparative. HPLC (Waters Xbridge C18 19×100 mm; Solvent A: 10% MeOH, 90% H2O, 0.1% TFA; Solvent B: 90% MeOH, 10% H2O, 0.1% TFA). The desired fractions were collected, concentrated and freeze dried using MeOH (0.3 mL) and water (0.7 mL) to yield 2-hydroxy-N-(2-hydroxyethyl)-2-(2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazol-7-yl)acetamide (0.014 g, 0.024 mmol, 35% yield) as a pale yellow solid. The compound had an HPLC retention time=3.53 min. (condition C); LC/MS M+1=516; 1H NMR (500 MHz, C3D6O) δ ppm 6.91-6.97 (2H, m), 6.82-6.90 (4H, m), 6.69-6.77 (2H, m), 4.62 (1H, d, J=4.4 Hz), 4.36 (1H, d, J=3.9 Hz), 3.18 (1H, OH, br. s.), 2.87 (2H, m.), 2.57-2.65 (2H, m).

Provenance & Evidence